Unconventional Advice For Entrepreneurs, Life Lessons, And The One Question I Ask Everybody

I loved the format and invited readers to send me a set of questions to answer in a similar way.

Alyssa Powell took me up on the offer (thanks!) and sent the following questions about everything from launching projects and entrepreneurial efforts, to relieving stress and feeling alive.

Q1: If you only had one question you could ask during every in-person interaction, what would it be?

“Is there some way I can help you?”

The best way to create value is to provide value.

I regularly ask people what they’re working on to figure out if there’s a way I can help them and there almost always is.

Whether it’s sharing advice, resources, or a connection to somebody else who can help them, it’s remarkable how many easy ways there are to help people — and amazing how many good things come from doing so.

Q2: What’s one moment you recall in life that you felt the most alive?

Twenty years ago I graduated college and drove cross country to move to Los Angeles where there was no job waiting for me and nobody I knew except for some distant family members who had offered to let me stay at their house until I got settled.

During that week-long trek through parts of this country I’d never seen before, I became hyper aware of what a unique moment it was.

It was a moment of zero responsibilities and commitments — no job, school, relationship, rent, bills, or anything beyond a theoretical need to get to Los Angeles at some point.

It was total and complete freedom and I knew it would be one of the only times in my life I’d be in that situation.

I enjoyed the hell out of it.

Q3: Despite the advice of putting your work and projects into the wild before they’re ready — is there something you’ve created that’s still waiting to be released?

Since I run a newsletter that’s all about the value of ideas, it’s probably no surprise I’ve got a ton of them that haven’t quite been unleashed on the world yet.

I have an idea file loaded with hundreds of ideas, links to interesting stuff, and partially (or fully) written drafts of blog posts at all times.

Q4: What’s one piece of nonconventional advice you have for entrepreneurs?

Don’t chase money.

If you become an entrepreneur solely because you want to become rich, it won’t happen.

Successful entrepreneurs are driven by a desire to create and provide value, solve problems for people, and correct inefficiencies in the world.

Money’s not a goal — it’s a byproduct of solving a problem.

Q5: Often times we forget to look up (we’re either focused, staring straight ahead or looking down at our phones) — what’s one thing you would’ve missed if you didn’t make an effort to look up?

It’s easy to focus so much on where you’re going that you forget to appreciate where you’ve been.

Q6: Pick one social media platform. What’s your audience’s overall persona and does this help with creating engaging content?

I don’t believe the audience persona changes across platforms — if you have a consistent brand, you attract a consistent audience.

But what changes is how your audience uses each platform.

For example, in my For The Interested Facebook group the audience is eager to engage with each other so the role of my content is to enable and encourage that — to spark interesting discussions among group members.

By comparison, on the For The Interested Instagram account, the audience is more passive. Presenting them with quick, inspiring ideas to consume as they endlessly scroll their feed works best.

Q7: What’s one event you’ve attended that meant the most to your personal or career development?

A decade ago, back when you still had to convince people that social media mattered, I went to a conference called Blog World for several years in a row.

Each year I’d attend panels there featuring speakers who were experts in online content and marketing.

I’d furiously take notes, then return to my job (which at the time was running content and marketing for a comedy startup website) and test out all I had learned.

In retrospect, the combination of being exposed to those speakers and then being able to experiment and implement their advice immediately after during a time when social media was largely overlooked gave me a huge competitive advantage and catapulted my career.

I used to say the job of somebody who works in social media is to be two years ahead of the general public in terms of understanding the power of these tools — going to that conference was one of the ways I was able to do so.

(SIDE NOTE: As the years went on I found I learned less and less at that conference which made me realize my own expertise and skills had increased to the point where I knew about as much as the “experts” on stage. They didn’t get any dumber — I just got smarter. It was a clear way to measure my progress in the field.)

Q8: What are a few things you do to alleviate stress?

I go for a 30-minute walk every morning and often times do it again at night.

Sometimes I listen to podcasts during the walk, sometimes I listen to music — but every time I generate some of my best ideas during those walks and always feel less stressed after them.

I also notice when I play video games my brain completely shuts off from whatever else I would typically think or stress about while I’m playing.